Had been a long time lurker, but this topic really strikes close to my heart and I really have the urge to give my two cents. Please bear with me if my thoughts aren't too coherent.
A thread about Toronto-haters is so appropriate, because I was one of them. Well, never "hated" the city as intensely as those commenters on newspaper sites or certain posters on this forum, but was definitely frustrated and disappointed constantly by the things and people in the city. The infrastructure projects that never take off or, when they do, end up truncated or crappy; the inane politicians and bureaucracy (although this is also a problem on the provincial and federal levels); the NDP-unions machinery that hijacks and cripples every aspect of life and politics; etc. And I was certainly not alone among my peers. Admittedly, most (but not all) of them were first-generation immigrants who unwillingly followed their parents to this place, and their old homes were always an easy comparison. Even I, born in Toronto but spent a good portion of my early childhood in Hong Kong and Vancouver, always compared Toronto to Hong Kong and, invariably, Toronto always came short. Why do world-class skyscrapers pop up there like weeds while we were always stuck with tiny stubs? Why did we take 10 years to plan and build 5 km of subway under a road, while in the same amount of time they could complete almost 10 times that length of railway through mountains and sea and marshes and right through what is among the densest urban areas in the world? Regarding the attitude of disdain, or at least, indifference for Toronto, one of my friends put it best when he said during highschool that Toronto would merely be a stepping stone in his life, as nothing in the city was worthy of him staying. As for myself, I remember that when I came back to Toronto from a trip to Europe a couple years ago, there were a good number of European tourists (French, Belgian, German) on the plane, families and all, all appearing very excited on the plane and when they arrived at Peason. I was thinking to myself, "What possibly can they be excited about a trip to Toronto?"
After university graduation, a substantial fraction of my friends dispersed throughout Asia and North America for work or further study, and I myself also moved to Boston two years ago. Work/study opportunities certainly affected strongly where we ended up, but most of us did leave with a feeling of being fed up or simply having had enough of Toronto, or at least wanting to see how the rest of the world is like. For myself, my first year in Boston was definitely a grace period, when everything in this new home seems good, from the European-ness of the urban landscape, to the vibrancy of its young population, to the (relatively) extensive transit system. But as I learned more about Boston (and, about Toronto) through forums like this and its Bostonian counterpart, and actually paying more attention to news and analyses about urban development, the more I began to appreciate Toronto -- not an insignificant change in attitude on my part.
Torontonians complain about the slowness and ineffectiveness of the planning process, but Toronto's scale and level of development in the recent 5 years was light-speed compared to Boston's. For sure, huge mistakes were made here in mid-century, such as tearing down two entire downtown neighbourhoods and replacing them with suburbia-type development, or ripping apart the city with two immense aboveground expressways. Probably as a reaction to these mistakes, the process in Boston had slowed to a trickle in recent years. The consultation process is long and painful, and whenever a slightly admirable project is proposed, such as ones for, say, a 30-story mixed-use tower in downtown, it will be met with such inane (but highly respected and circulated) criticisms as "it's too tall", "it's out of context" or "it casts shadows". After 10 years of manoeuvering and slashing the building to perhaps 10 or 20 floors, construction will finally start, the old building will be demolished, just in time for a recession to come around, the project stalls, and leaves giant craters in the middle of the city. Transit planning turns out to be not much better either. While in Toronto at least we get to debate whether to build subways vs. LRTs, all the hype and debate here right now is about a couple plans, decades in the making, to spend a few billion dollars to build a few kms of tunnels for BUSES, to be part of this "futuristic" and totally new-fangled "BRT" network the majority of which will be running in mixed traffic. And mind you, this is not some Rust Belt auto-centric city with a dismal transit system but one of the most well-utilized urban rail transit network in North America.
For sure, Boston is not the perfect comparison for Toronto because it is a smaller city, but its aspirations (or credentials, which are not minor) to be a world-class city is every bit as big or in fact bigger than Toronto. The civic pride here no doubt is built largely from its history, its institutions, its sports teams and, not least, NYC-hating, but on Bostonian forums and newspaper sites, negative feelings towards the city's problems and (lack of) progress are just as strong as Toronto. And it's not necessarily a bad thing, because genuine concern and constructive criticisms for the citizens' own city are instrumental in ensuring the continued progress and viability of the city. But criticisms need to be accompanied by two things to be healthy: perspective and pride (not baseless and unrealistic flattery of absolutely everything in the city, but a true appreciation of the progress we have made). Pride is probably harder to build in the short term, to a large extent because Toronto hasn't "gone through" as much as many other major cities in the world. It's hard to deny that Toronto doesn't have much to talk about in our history, perhaps other than being looted and burned by the Americans in 1812, compared to cities like Boston that was the site of so many events throughout American history. And for those above who mentioned Hong Kong while saying Toronto is a young city, Hong Kong is a younger city, but it has gone through much, much more, being among the most important players in 19th and 20th century Chinese history and among the major theatres for two revolutions, a world war, and Sino-British, Imperialist-Republican and Communist-Nationalist struggles. All these contributed to Hong Kong's intense civic pride, and Toronto must make do with never having the "luxury" of going through such events to help consolidate a civic identity.
The other point, perspective, is as I have described above regarding my realizations after having spent time in another city and also to learn about the real inner workings of other cities. Boston obviously had all the problems I mentioned above and many more societal problems, exemplified by shoot-outs in the middle of downtown in broad daylight, despite being one of the safest cities in the US. Hong Kong, while having an amazing progress in development that is still jawdropping by any measure, achieved it largely by an extremely unhealthy, corporate-centric development model that rammed projects through at the expense of many other considerations, and Hong Kong society itself is sick to the core in many ways. Nowadays, whenever I talk to Americans who have been to Toronto, they have nothing but praise for our city. Recent things that I've heard include "Oh Toronto, the New York of Canada; or perhaps New York is the Toronto of America"; or "Toronto is like a New York that's more civlized". Every city has their problems, and it will really take an open, objective and willing mind to learn about the true merits and shortfalls of each city.
Back to my anecdote. As a proof of the point that comparison can really change one's views, even after just a couple short years, many of my friends who have moved away from Toronto now yearn to go back / have already gone back, as soon as their degree or their current job is finished, or at least as a wish for sometime in the unforseeable future. As for myself, nowadays when my American friends tell me they are planning a trip to Toronto and ask me what is there to see and do, sometimes I am still at a loss about what to suggest, but at least I am starting to put myself in the shoes of a non-Torontonian and come to see things that would, indeed, impress or at least be interesting to others, things that may indeed make me feel "proud" of my own city. I have definitely come to feel more proud of Toronto nowadays, more appreciative of her rapid progress that I have witnessed even within my teens, and more genuinely concerned about her future. Of course, all the old problems still exist, and I am still not sure where I will end up next after Boston (Europe would be nice), but my ranking of Toronto has definitely risen quite a bit compared to when I left.
And for the friend who was using Toronto as his stepping stone, well, he's still in Toronto enjoying life.
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wow that was a long post.. sorry..